7 Things We Expect President Obama Will Do on O‘ahu

After seven consecutive Hawai’i vacations, President Barack Obama is spending Christmas on O’ahu with his family this month once again. Here’s what to expect.


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5. Secret Service

The Secret Service wouldn’t give us any information for this story (understandably), but all the folks we spoke with had nothing but nice things to say about the men and women who would lay down their lives for the president and his family.


“You’d think they’d get tired of their job, wanding people. They’re so kind about it, and they’re not pushy or arrogant,” says Duprey, who has interacted with the Secret Service every year the president has been in town. “They are so gracious. I’ve been impressed by running into them.”


Duprey says that, while on O‘ahu, you’ll see agents in sport slacks and high-end aloha shirts, such as ʻIolani and Tori Richard. Still, they don’t exactly blend in. “On Christmas morning, I was walking my dogs on Kailua Beach and there were all these guys who were trying to look like surfers on Kailua Beach, but you know that they’re Secret Service and they’re all talking into their watches,” says Duprey with a laugh.


6. An Obama Christmas

It wouldn’t be Christmas for the Obamas without a few family holiday traditions (one of them being presidential pie after dinner). For Michelle, the season of giving begins on Christmas Eve when she fields calls for the North American Aerospace Defense Command (NORAD) Tracks Santa program. The FLOTUS answers phone calls from children all over America wondering where Santa is on his gift-giving expedition. As she follows NORAD’s online tracking of Saint Nick and his sleigh, she asks kids what they want for Christmas and tells them to go to sleep early. “And you know how many gifts he’s delivered already?” she asked a 5-year-old boy from North Carolina last year.


“No, maam.”


“More than 3 billion gifts he’s already delivered. Isn’t that something?”


Kids and parents who get to speak to Michelle for a few minutes are elated. The president then calls U.S. armed-forces members around the world, thanking them for their service and wishing them happy holidays.


Kailua home, while the afternoon is spent with friends and the troops at MCBH. Obama poses for photos, signs autographs and speaks to them over their dinner before having his own with the first family. The White House often releases the Obama Christmas dinner menu, and it always includes pie. “There is no holiday dinner that does not end with pie, be it sweet potato, apple, pumpkin or banana cream,” said Sam Kass, a White House assistant chef, in an email interview with Politico. Kass often accompanies the Obamas on their holiday vacations, preparing their meals when they’re not dining out.


7. The Neighborhood

A surefire sign that Obama’s in town is the gunboats that appear in Kawainui Canal. For the duration of the presidential vacation, the U.S. Coast Guard sets up a security zone in the waters around the Paradise Point Estates peninsula, the exclusive Kailua neighborhood where the president has stayed for the past five years. This keep-out area includes about a half mile of the canal, a waterway popular among paddlers and a small slice of Kailua Bay, including part of a surfing area once known as Castle’s but now called Obama’s. (Where can you not surf when Obama’s here? Obama’s.) Violators face a $40,000 fine, up to 10 years in prison and, according to one Kailua resident who lives along the canal and hasn’t quite come to terms with the firepower that accompanies the leader of the free world, “possible death.”


Security within the Paradise Point neighborhood has gotten tighter since Obama first stayed there as president-elect in 2008. Initially, neighbors gathered on the sidewalks to greet Obama’s motorcade as it passed, and gawkers routinely drove into the neighborhood to see what they could see. More recently, the neighborhood has been closed to all but its residents and their registered guests, and nobody’s allowed on the sidewalk when the motorcade drives by.


The last hundred yards or so at the north end of Kailua Beach are also closed, with congenial Secret Service officers in khakis and aloha shirts turning away beach walkers, whose numbers always swell when the winter White House comes to O‘ahu. A handful of Obama haters inevitably grumble about traffic backing up when the motorcade passes and how “Obama closed the ocean.” But Kailua, for the most part, takes it all in stride.


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Honolulu Magazine September 2018
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